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Sinatra's gangster image was more about 'being a wannabe, an idolator, than any actual mob affiliation'

In "Empire State of Mind," Jay-Z declared that he's "the new Sinatra." And in a New York Times op-ed, writer James Kaplan argues that Jay's assertion that Sinatra had "a little tougher [upbringing] than mine" is wrong. Kaplan, author of the recent Sinatra biography The Voice, writes: "In fact, Jay-Z, who grew up with a single mother in the drug-and-bullet-riddled Marcy housing projects in Brooklyn, had a much tougher youth than Frank Sinatra, who was the only child of upward-striving, financially comfortable parents in Depression-era Hoboken, N.J."

The article — which was published to commemorate what would have been Sinatra's 95th birthday — further examines connections between the late singer and hip-hop. "Sinatra's unfortunate flirtations with the Mafia later on — much like the gangsta affectations of many rappers — had more to do with being a wannabe, an idolator, than any actual mob affiliation," Kaplan writes. (In his new memoir, Decoded , Jay discusses his days as a drug dealer at length.)

Yet that affectation, Kaplan argues, was far from Sinatra's greatest strength — in fact, the opposite was. Sinatra's "vulnerability is at the core of his magic," he writes. "There was an operatic intensity to Frank Sinatra's existence. ... The conflicts filter into the molecules of his music. We hear, we respond." Indeed, he writes that Eminem's "Not Afraid" is a stellar example of how the best rappers attain a similar goal, exposing "the sorrow and humanity that underlie the swagger."